>>40832620Ash growing out of his cockiness, pride and asshole qualities was good by itself, showed character progression, culminating in beating the Orange League, and later Gary.
THE PROBLEM was making it an enternal series, with Ash staying the protagonist past Johto, when he's pretty much learned all his lessons by the end of the Original Series. They really should have left Team Rocket as the "link" between the series, and instead make Brendan and May new protagonists without Ash, who'd instead reappear as a recurring "mentor" trainer (which he was to May and Dawn anyway) and to promote FRLG.
Now Ash has nowhere to progress as a person. At his worst he can be a bit too carefree, or take (some) losses too seriously. The only time he's been challenged as a person post-Johto was in his confrontation vs Paul.